Sissy World Stories

141,036 results
Orientation
Length
Source
Infinite Scroll

Robin and Jimmy Olsen - Sissies Ch. 06

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

"Miss Robin! Surely you can't be serious!" "Introduce us, Alfred! Just like any other guest arriving, we deserve to be introduced to the crowd!" demanded the lovely sissy! Robin and Jamie were dressed in very attractive summer dresses - Robin in blue and Jamie in green which accentuated his green eyes and emphasized his bright red hair! The dresses would ha...

Fantasy to Reality

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness. My body was numb and I waded through a sea of words and images that filled my mind, struggling to focus on anything specific. Slowly I began to wake but my eyes did not open and my body remained numb. I searched for my memory, I knew it was there but I couldn't reach it, I was entranced. My name and past eluded me as I s...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Sissy Lesbian Rita Meets Lisa

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my two already published stories: 'Miss Johnstone's Lesbian Sissy Slut' and 'Further Training as Sissy Lesbian'. I sincerely recommend reading these stories first as it provides background for this one. My stories have been well received and I would like to thank you all for the positive response! Enjoy and please ta...

A Sissy's Life

by Queen_Diana on Jan 27, 2020
Fetish

A Sissy’s Life by Queen Diana Slutty pink lip gloss? Check. Ass cheeks practically hanging out of a scandalously short pink skirt? Check. Pink tube top, butt plug, and thigh high stockings? Check. “Check, check, and check! That’s everything!” I giggle. Looking over at the body length mirror. Writhing with satisfaction, as I realize, what a pretty little sis...

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The Dominatrix Order Pt. 02 Ch. 04

by Jwwsmith on Feb 11, 2019
Transgender & Crossdressers

Protestors swarmed the streets of Femininus on what was the anniversary of the initial passing of the 23rd Law. It had recently been considered for repeal and been upheld by the Council of Goddesses. The protestors demanded that the 23rd Law be repealed and that same sex courtship be legalized. The predominantly liberal crowd congregated before the steps of...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...

Angel Learns My Secret

by Angelscuck on Sep 16, 2017
Loving Wives

My wrists strained at the ropes that bound me to the chair. The vibrator taped to my cock was driving me mad while I watched my leather clad bride mount her lover's huge black cock. Angel smiled at me teasingly, knowing the pleasure and pain I was experiencing.... Suddenly I heard her key in the door I quickly turn off the magic wand, put it in the desk dra...